Carbon tetrabromide → HCID 57544367, compound

HRID 537983Notes

Reaction equation

HRID 537983 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.[I:25][C:26]1[C:27](CO)=[CH:28][C:29]2[C:34]([CH:35]=1)=[CH:33][CH:32]=[CH:31][CH:30]=2>C(Cl)Cl>[Br:24][CH2:20][C:27]1[C:26]([I:25])=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 148134243-Iodo-2-naphthalenemethanol

Product 1

HCID 57544367HCID 57544367, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triphenylphosphine (469 mg, 1.79 mmol) in dry CH2Cl2 (2 mL) was added dropwise to a stirred solution of carbon tetrabromide (592 mg, 1.79 mmol) and (3-iodo-2-naphthyl)methanol (423 mg, 1.49 mmol) in dry CH2Cl2 (11 mL) at room temperature under N2. The reaction was stirred for 4 h at room temperature and was concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 25×160 mm, 0-50% EtOAc in hexanes gradient) to afford 2-(bromomethyl)-3-iodonaphthalene (469 mg, 91%), as a colorless solid. Rf=0.84 (20% EtOAc/hexanes). 1H NMR (600 MHz, CDCl3): δ 8.39 (s, 1H); 7.94 (s, 1H); 7.78-7.76 (m, 1H); 7.71-7.69 (m, 1H); 7.52-7.48 (m, 2H); 4.76 (s, 2H).

Workup

  1. concentrationwas concentrated in vacuo
  2. customto give the crude product
  3. customThis was purified by flash chromatography (Si, 25×160 mm, 0-50% EtOAc in hexanes gradient)

Sources & evidence

ORD record
ord-3473d7f00e944c0fb02a59f67462a97a
Source dataset
uspto-grants-2014_10
Patent number
US08865707B2

Reaction notes

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